Office Bet Stories

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The Summer Internship Ch. 04

by ynglady22 on Aug 30, 2017
Interracial Love

Alisha walked into work hoping that her facial expression did not look like she had been having sex the night before and this morning. She just felt so relaxed. While her pussy definitely was bruised from the hard sex Thomas had put on her, she still felt good. She soon pictured Thomas in her mind. He was so sexy to her. Just looking at him would make her ho...

Caught Masturbating

by ky_fella_57 on Sep 16, 2017
Toys & Masturbation

Caught Masturbating While Thinking about the Office Slut On this day at work, I spent way too much time thinking about a female co-worker. Her name is Nerissa and she is a legal secretary. Nerissa had joined the firm as a secretary a little over two years ago. Her workstation is outside my office and I can see her come and go all day long. She is in her mid...

The Fourth Floor of a College Dorm

on Dec 21, 2016
Erotic Couplings

You throw on a red t-shirt and do up your jeans. You know tonight's a big night, lots of chances to make good with the ladies on the floor. You check yourself out in the mirror and figure that you're looking about as good as you're ever going to. You received the unique luxury among the people of your floor through a fluke of paperwork that never got correct...

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The job at Jenkins park

by CarrieQ on Mar 31, 2020
Transgender & Crossdressers

For several years, I lived and worked in a sleepy little town. It suited me just fine, being clean, quiet and close to the city. The locals were friendly enough and, more importantly, they didn't know my history. Looking back, I'd say one or two of them had maybe guessed I was trans, only they were too polite to let on! This was before the Gender Recognitio...

Porn Job

by Penny_Tralia on Sep 1, 2017
Group Sex

I needed a job so I took it. I’d never worked for a porno film company, but what the hell, it was a job and I needed the money. My boss, David was nice enough. Never made any kind of pass at me and never made any sexual comments to me, so it was just like working in any office. Except that the people coming in were all porno stars or had something to do with...

Caught by My Boss

by Sabineteas on Sep 11, 2017
Exhibitionist & Voyeur

I can't believe that I was so stupid! It was just a stupid dare and bet. Something that I would never have done if we hadn't been drinking that night. But all of you know that alcohol is never a good thing when you end up doing something that you shouldn't. And because I was drinking, because my friends dared me and even bet me a month's rent on my apartment...

The Bet Ch. 03

by MutableMalachi on Sep 15, 2017
BDSM

Allan released me from the bonds connecting me to the Cross, supporting me as I stepped free. I tried to shake him off, insisting I was fine - the whole scene had only lasted a few minutes, and I hadn't done anything - but he held firm. Once we started to walk, I realized to my embarrassment that I was not fine. My knees felt like jelly and my head swam. Cha...

Deadhead

by rhj4 on Dec 12, 2018
Exhibitionist & Voyeur

When I first saw her dancing at the Grateful Dead concert, she looked somehow familiar. But it wasn't that deja vu feeling that attracted me to her; it was her naked boobs bouncing in the afternoon sunshine as she danced and pranced to the music. She was in the middle of a crowd of thousands, and I was only about 20 feet away; but she might as well have be...

Andee Loses Another Bet

by AndeeLicious on Sep 12, 2017
Loving Wives

It had been a long time in coming. Andee wasn't sure if having to "pay up" for losing a friendly bet with her co-worker was just a passing joke in the hallway, or if he was serious about collecting on it. As a 38-year old mom of two very active boys and career woman, she enjoyed a bit of adventure in her life and this was the second time in a year she had fo...

True Blue Ch. 3

by Stiffness on Sep 16, 2017
Interracial Love

Rocky was in a state of shock. He paid off on the bet and I chuckled to myself as he tried to rationalize his wife's behavior. "I still can't believe Leesa jacked that fat fuck off," he said. "I know she would never have done that except I think she was confused by the phone call and all. Besides, I think she was probably impressed by the size of Willy's coc...